the best artists bring something to the table their listeners didn't see coming.
like, in 1993 you couldn't ask a future 2pac fan, before he came out with all eyez on me, who would go on to be a lifelong 2pac fan to describe an artist similar to what 2pac would become. 2pac had to do what nobody knew to ask from him to do what he did.
i look for artists that are aware of what they do well, because if they're aware of what they do well, they'll be able to form a strong catalog and keep progressing — which means they'll be worth listening to for a while. a lot of artists show glimmers of brilliance but they don't know how to replicate it and take it further each time they step in the booth.
best example i have is husalah — as far as music (casting the beef, allegations and drama aside), the shit he was making before he went in was dope, on a strictly music level it's hard to deny. to me it seems he didn't understand his craft enough to keep that going and take it even further and now he plays soccer or some shit.